


Holiday Gathering

by Thrillhouser



Series: Cheating Stiles Stilinski [3]
Category: Teen Wolf (TV)
Genre: Anal Fingering, Anal Sex, Blow Jobs, Bottom Jackson Whittemore, Cheating Stiles Stilinski, Filming, Innocent Derek Hale, M/M, Masturbation, Plot What Plot/Porn Without Plot, Top Stiles Stilinski, Underage Sex, Video Cameras
Language: English
Status: Completed
Published: 2020-12-23
Updated: 2020-12-23
Packaged: 2021-03-11 01:28:58
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 1,159
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28266906
Author URL: https://archiveofourown.org/users/Thrillhouser/pseuds/Thrillhouser
Summary: Stiles slips out of a Christmas movie date with Derek to study with Jackson. Their study session is captured on camera.
Relationships: Derek Hale/Stiles Stilinski, Stiles Stilinski/Jackson Whittemore
Series: Cheating Stiles Stilinski [3]
Series URL: https://archiveofourown.org/series/2053872
Kudos: 45





	Holiday Gathering

**Author's Note:**

> Thoughts? This is part three of Stiles accumulating sluts. I'm still taking suggestions on who should be next.

It was almost midnight when Jackson’s eyes lost a little focus, a bead of sweat ran down from his temple to his pecs, down his abs, and he stayed on his knees, jerking off furiously, drifting in and out of focus on the small screen of his camera - borrowed from Matt. The bed beneath him was in disarray, a messy reminder of what had been captured on camera. While he pinched one nipple, Jackson worked over his dick. On the screen, Jackson faced the camera, his face blissed out and unfocused, and the clean line of his toned back led to a head eating him out. Jackson moaned in unison to the sinful sounds slipping through Jackson’s lips on screen.

Jackson remembered the tongue spearing into him, the hands that held his ass apart, the slight moaning from behind him, the feeling when he reached back with one hand to push the other teen deeper in. He could feel his own hand, then and there, tugging on his cock, his excitement and precum. Bringing the camera with him, he lay back against the bed, on leg over the bed and the other spread wide. When Stiles stood back up, he ran his large dick over Jackson’s hole, emphasizing the size he would sink into the star athlete seconds later.

“What do you want Jacks? You make such pretty sounds, do you talk pretty too?”

As Stiles and Derek sat on the couch earlier that evening, they curled up together to watch A Muppets Christmas Carol. As silly as the movie is, it had been a tradition of Derek’s to watch it every year a few weeks before the holiday, and to watch A Charlie Brown Christmas on Christmas morning with a Bailey’s and coffee. Derek kept the tradition since his childhood, a remnant of times with his sister and mother, a carryover from the holidays. Stiles grabbed the last small slice of cake from the table, he was unable to resist sweet temptations.

Jackson texted to gently and subtly remind Stiles about working on their class project with a curt, “wru?” and Stiles sighed. While Stiles leaned up back against his boyfriend, legs crossed , Derek’s legs were spread wide, and his arms engulfed the smaller framed man. Ebenezer Scrooge hadn’t been redeemed yet, he hadn’t faced his evil deeds, and Stiles would never learn the true meaning of December thirteenth - until they invariably came across another adaptation. Derek smoothed Stiles’ short hair, kissed him on the back of his head, knowing full well the teen had to dash before Scrooge was redeemed.

Pulling into the driveway, he approached the door and found Jackson waiting at the door - “didn’t I tell you to park on the street? I don’t want the neighbors seeing that thing.” “Dude, there’s no one here. Your parents are out, who gives a shit?!” Jackson tested Stiles’ patience, but they both knew where the evening would end up.

Cock right up against Jackson’s hole, “So baby, what do you want me to do to you?” Jackson saw his face in the camera screen, the pupils dilated, his mouth ajar and face beading with sweat, and his hair in uncharacteristic disarray, he looked fully fucked out. Touching his lips, he knew the lips were dry and chapped from having blown Stiles. Only lube you’ll get, baby, is your spit, Stiles had muttered to Jackson. Jackson couldn’t bring himself to answer Stiles’ question, but Jackson knew Stiles wanted an answer.

“C’mon Jacky, you gotta tell me,” Stiles teased Jackson again, pushing the tip against Jackson’s hole, canting his hips forward, against the other man.

“Just fuck me, Stiles. Fuck me please!”

With that, Stiles spat in his hand, coated his dick, and pushed in.

While still on his knees, Jackson - the real Jackson - thrust in time with Stiles. It was so fun to watch his own facial expressions, the joy and mischief and glee radiating off Stiles’ face. He couldn’t help but be enraptured with the scene that had played out a few hours prior, his free hand’s fingers pressing into his chest, working down the line of his hard-earned abs, down below his balls, reaching for the still sore hole.

Bringing his hand swiftly to his mouth, he sucked in three fingers, and then brought them back to push into his hole. The sting, the wince of pain, that was worth it to emulate the pleasure on screen. When Stiles would push in, hard, he would thrust Jackson forward and back, the screen capturing Jackson biting his lip, the wanton desire for more, faster, harder, and the callous lengths he would push himself through to please himself, to Derek’s detriment. Stiles and Jackson pushed against one another in a symbiotic rhythm, both lead further and further along towards the same goal.

Stiles pulled out. “Jackson, I want you to ride me.” Grabbing one of Jackson’s pillows, Stiles pushed forward, legs draped over the edge of the bed, the pillow supporting his head, as Jackson faced away from him - and thankfully towards the camera. Pushing down, he took Stiles to the hilt, establishing a rhythm, canting his hips, while showing for the camera his abs, taut muscular body, and obvious hunger for Stiles’ dick. Jackson couldn’t help himself, the noises he would make, the feeling of that large dick scraping up against his prostate, the moan he made when Stiles slapped his ass hard, the sensations fully coalesced into a sum more than its parts.

As Jackson watched himself, and Stiles’ huge dick plunging in and out, he was himself getting more and more lost in his own imaginings, musings, and desire for more. He fingers plunging in, his other hand tugging himself along, he could feel a steady heat build and his balls tightened. He was close. So close.

Stiles grabbed Jackson’s dick from behind - “Jacky, baby, I need you to cum.” Stroking him, slowly, steadily, Stiles built a rhythm to match the methodical rhythm Jackson employed while fucking himself on the smaller boy.

The camera screen showcased Stiles stroking Jackson and Jackson fucking himself on him, while the real Jackson fucked himself hard, pushing into himself with his fingers. Jackson couldn’t help himself, the heat had built up for a long time, the stinging pain that hurt so good, he was enthralled, enraptured by Stiles’ actions on cam.

In one, two, three shots, Jackson’s cum shot splattering on the bedspread beside him, on his hips and some on his thigh. His eyes lost focus, his breathing rapid, as the scene continued to play out on his camera. By that point, Stiles had pushed Jackson off his cock, and was on his knees feeding Jackson his load.

When Stiles returned to Derek’s place, sated and happy, a chocolate babka in hand as an apology for missing their date, Derek was half sleeping through the original Grinch. For someone so dour, he certainly held to his holiday traditions.


End file.
